US11339143B2ActiveUtilityA1
Condensed cyclic compound and organic light-emitting device including the same
Est. expiryJun 26, 2038(~12 yrs left)· nominal 20-yr term from priority
C07D 405/14C07D 487/04C09K 2211/1044C07D 519/00C07D 401/14C09K 2211/1059C07D 409/14C09K 2211/1088C07D 491/04C07D 487/14C07D 491/153C07D 495/14C09K 2211/1007C07D 495/04C09K 2211/1037C07D 491/048C07D 403/14C09K 11/06C09K 2211/1029C09K 2211/1092C07D 491/147C07D 401/10C07D 403/10C09K 2211/1033H01L 51/0074H01L 51/0072H01L 51/5012H01L 51/0073H01L 51/0067H10K 85/6572H10K 50/12H10K 85/6576H10K 85/6574H10K 85/654H10K 2101/20H10K 50/11H10K 85/657
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Claims
Abstract
A condensed cyclic compound represented by Formula 1:wherein, in Formula 1, A1, D1, and R11 to R14 are the same as described in the specification.
Claims
exact text as granted — not AI-modifiedWhat is claimed is:
1. A condensed cyclic compound represented by Formula 1:
wherein, in Formulae 1, 2, and 3-1 to 3-5,
D 1 is a group represented by Formula 2,
A 1 is a group represented by one selected from Formulae 3-1 to 3-5,
R 11 and R 12 are each independently a substituted or unsubstituted C 6 -C 30 aryl group,
A 21 and A 22 are each independently selected from a benzene group, a fluorene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, an indolofluorene group, an indolocarbazole group, an indolodibenzofuran group, an indolodibenzothiophene group, an indenofluorene group, an indenocarbazole group, an indenodibenzofuran group, an indenodibenzothiophene group, a benzofuranofluorene group, a benzofuranocarbazole group, a benzofuranodibenzofuran group, a benzofuranodibenzothiophene group, a benzothienofluorene group, a benzothienocarbazole group, a benzothienodibenzofuran group, and a benzothienodibenzothiophene group,
X 31 is N or C(R 31 ); X 32 is N or C(R 32 ); X 33 is N or C(R 33 ); X 34 is N or C(R 34 ); X 35 is N or C(R 35 ); X 36 is N or C(R 36 ); X 37 is N or C(R 37 ); and X 38 is N or C(R 38 ), wherein at least one selected from X 31 to X 35 in Formula 3-1 is N, and at least one selected from X 36 to X 38 in Formulae 3-2 to 3-5 is N,
Y 31 is selected from O and S,
R 13 , R 14 , R 21 , R 22 , and R 31 to R 39 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, a substituted or unsubstituted C 7 -C 60 aryl alkyl group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted C 1 -C 60 heteroaryloxy group, a substituted or unsubstituted C 1 -C 60 heteroarylthio group, a substituted or unsubstituted C 2 -C 60 heteroaryl alkyl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q 1 )(Q 2 )(Q 3 ), —N(Q 4 )(Q 5 ), and —B(Q 6 )(Q 7 ),
two neighboring groups selected from R 31 to R 39 are optionally linked to form a condensed ring,
b21 and b22 are each independently selected from 1, 2, 3, 4, 5, 6, 7, and 8,
b39 is selected from 1, 2, 3, and 4,
Q 1 to Q 7 are each independently selected from hydrogen, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group,
provided that when A 1 is a group represented by Formula 3-1 and R 21 or R 22 is N(Q 4 )(Q 5 ), then Q 4 and Q 5 are each independently selected from hydrogen, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group,
provided that when A 1 is a group represented by Formula 3-1, then R 11 and R 12 are each independently selected from:
a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, and a chrysenyl group; and
a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, and a chrysenyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, and a phenyl group, and
ii) R 13 and R 14 are each independently selected from:
hydrogen, deuterium, —F, —Cl, —Br, —I, a cyano group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, and a chrysenyl group; and
a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, and a chrysenyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a cyano group, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, and a phenyl group, and
* indicates a binding site to a neighboring atom.
2. The condensed cyclic compound of claim 1 , wherein
R 11 and R 12 are each independently selected from:
a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, and a chrysenyl group; and
a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, and a chrysenyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a cyano group, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, and a phenyl group.
3. The condensed cyclic compound of claim 1 , wherein
R 11 and R 12 are each independently selected from:
a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group; and
a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group, each substituted with at least one selected from deuterium, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an iso-pentyl group, a sec-pentyl group, a tert-pentyl group, an n-hexyl group, an iso-hexyl group, a sec-hexyl group, a tert-hexyl group, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, and a phenyl group.
4. The condensed cyclic compound of claim 1 , wherein
A 21 is a benzene group, and
A 22 is selected from a benzene group, a fluorene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, an indolofluorene group, an indolocarbazole group, an indolodibenzofuran group, an indolodibenzothiophene group, an indenofluorene group, an indenocarbazole group, an indenodibenzofuran group, an indenodibenzothiophene group, a benzofuranofluorene group, a benzofuranocarbazole group, a benzofuranodibenzofuran group, a benzofuranodibenzothiophene group, a benzothienofluorene group, a benzothienocarbazole group, a benzothienodibenzofuran group, and a benzothienodibenzothiophene group.
5. The condensed cyclic compound of claim 1 , wherein
two or three selected from X 31 to X 35 in Formula 3-1 are each independently N, and two selected from X 36 to X 38 in Formulae 3-2 to 3-5 are each independently N.
6. The condensed cyclic compound of claim 1 , wherein
R 13 and R 14 are each independently selected from:
hydrogen, deuterium, —F, —Cl, —Br, —I, a cyano group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, and a chrysenyl group; and
a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, and a chrysenyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a cyano group, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, and a phenyl group.
7. The condensed cyclic compound of claim 1 , wherein
R 21 and R 22 are each independently selected from:
hydrogen, deuterium, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a pyrrolyl group, a furanyl group, a thiophenyl group, an indolyl group, a benzofuranyl group, a benzothiophenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a naphthobenzofuranyl group, a naphthobenzothiophenyl group, a dibenzocarbazolyl group, a dinaphthofuranyl group, a dinaphthothiophenyl group, an indolocarbazolyl group, an indolodibenzofuranyl group, and an indolodibenzothiophenyl group; and
a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a pyrrolyl group, a furanyl group, a thiophenyl group, an indolyl group, a benzofuranyl group, a benzothiophenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a naphthobenzofuranyl group, a naphthobenzothiophenyl group, a dibenzocarbazolyl group, a dinaphthofuranyl group, a dinaphthothiophenyl group, an indolocarbazolyl group, an indolodibenzofuranyl group, and an indolodibenzothiophenyl group, each substituted with at least one selected from deuterium, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, a biphenylcarbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group.
8. The condensed cyclic compound of claim 1 , wherein
D 1 is represented by one selected from Formulae 2-1 and 2-2:
wherein, in Formulae 2-1, 2-2, 9-11, 9-21 to 9-23, and 9-31 to 9-48,
A 21 is a group represented by Formula 9-11,
A 22 selected from groups represented by Formulae 9-11, 9-21 to 9-23, and 9-31 to 9-48,
C 1 to C 4 are each independently a carbon atom,
X 91 is selected from O, S, N(R 22d ), and C(R 22d )(R 22e ),
X 92 is selected from O, S, N(R 22f ), and C(R 22f )(R 22g ),
R 22a to R 22g are each independently the same as described in connection with R 22 in Formula 2, and
b22a to b22c are each independently the same as described in connection with b22 in Formula 2.
9. The condensed cyclic compound of claim 1 , wherein
A 1 is represented by one selected from Formulae 3-11 to 3-35:
wherein, in Formulae 3-11 to 3-35,
Y 31 , R 36 to R 39 , and b39 are each independently the same as in Formulae 3-1 to 3-5, and
* indicates a binding site to a neighboring atom.
10. The condensed cyclic compound of claim 1 , wherein
the condensed cyclic compound represented by Formula 1 is represented by Formula 1-1:
wherein, in Formula 1-1,
D 1 , A 1 , R 11 , and R 12 are each independently the same as in Formula 1.
11. The condensed cyclic compound of claim 10 , wherein
D 1 is represented by one selected from Formulae 2-1 and 2-2, and
A 1 is represented by one selected from Formulae 3-11 to 3-35:
wherein, in Formulae 2-1, 2-2, 9-11, 9-21 to 9-23, 9-31 to 9-48, and 3-11 to 3-35,
A 21 is a group represented by Formula 9-11,
A 22 is selected from groups represented by Formulae 9-11, 9-21 to 9-23, and 9-31 to 9-48,
C 1 to C 4 are each independently a carbon atom,
X 91 is selected from O, S, N(R 22d ), and C(R 22d )(R 22e ),
X 92 is selected from O, S, N(R 22f ), and C(R 22f )(R 22g ),
R 22a to R 22g are each independently the same as described in connection with R 22 in Formula 2,
b22a to b22c are each independently the same as described in connection with b22 in Formula 2,
Y 31 , R 36 to R 39 , and b39 are each independently the same as described in connection with Formulae 3-1 to 3-5, and
* indicates a binding site to a neighboring atom.
12. The condensed cyclic compound of claim 1 , wherein
the condensed cyclic compound represented by Formula 1 is selected from Compounds 1 to 1030:
13. An organic light-emitting device comprising:
a first electrode;
a second electrode; and
an organic layer disposed between the first electrode and the second electrode,
wherein the organic layer comprises an emission layer, and
wherein the organic layer comprises at least one condensed cyclic compound of claim 1 .
14. The organic light-emitting device of claim 13 , wherein
the first electrode is an anode,
the second electrode is a cathode,
the organic layer further comprises a hole transport region disposed between the first electrode and the emission layer and an electron transport region disposed between the emission layer and the second electrode,
wherein the hole transport region comprises a hole injection layer, a hole transport layer, an electron blocking layer, or any combination thereof, and
wherein the electron transport region comprises a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.
15. The organic light-emitting device of claim 13 , wherein
the emission layer comprises the condensed cyclic compound.
16. The organic light-emitting device of claim 15 , wherein
a ratio of a fluorescence emission component to a total emission component emitted from the emission layer is 90% or more.
17. The organic light-emitting device of claim 15 , wherein
the condensed cyclic compound is a fluorescence emitter, and
a ratio of an emission component emitted from the condensed cyclic compound to a total emission component emitted from the emission layer is 80% or more.
18. The organic light-emitting device of claim 17 , wherein
the emission layer consists of the condensed cyclic compound; or
the emission layer further comprises a host.
19. The organic light-emitting device of claim 15 , wherein
the emission layer comprises a host and a dopant,
the host comprises the condensed cyclic compound,
an amount of the host is larger than an amount of the dopant, and
a ratio of an emission component of the dopant to a total emission component emitted from the emission layer dopant is 80% or more.
20. The organic light-emitting device of claim 15 , wherein
the emission layer comprises a host, an auxiliary dopant, and a dopant,
the auxiliary dopant comprises the condensed cyclic compound, and
a ratio of an emission component of the dopant to a total emission component emitted from the emission layer is 80% or more.Cited by (0)
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